Who Were Tupac Shakur’s Girlfriends? His Secret Flings With Madonna, Jada Pinkett Smith & Lisa Lopes Unpacked

Who Were Tupac Shakur’s Girlfriends? His Secret Flings With Madonna, Jada Pinkett Smith & Lisa Lopes Unpacked

Rapper Tupac Shakur will always be remembered as one of the most influential artists of our generation. The All Eyez On Me hitmaker won fans over with his sick bars and strong character, traits which also attracted the ladies. From Jada Pinkett-Smith to Madonna, Briefly News shines a spotlight on the rapper's most infamous relationships.

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Tupac, 2Pac, Madonna, Jada Pinkett Smith, Will Smith, Lisa Lopes, Left Eye, Relationships
Tupac Shakur dated Madonna and Jada Pinkett Smith. Images: Getty
Source: Getty Images

Jada-Pinkett Smith meets Tupac in high school

Way before the fame and success, Jada Pinkett-Smith and Tupac Shakur were just two aspiring artists at the Baltimore School for the Arts in Maryland, USA. In the early 1980s, the students hit it off in between their endless classes and became instant friends.

Born on 16 June 1971 in New York, Tupac's parents were both activists and Black Panther members. The rapper grew up poorer than most kids in his neighbourhood but had an infectious charm that drew people in even then.

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Jada and Tupac met on the first day of high school when the confident boy approached her:

"Pac was a little funny looking. Definitely from looking at him, wasn’t necessarily the type of cat that I would even like, deal with...But as soon as he approached me, he was like a magnet. Once you paid attention to him he kind of sucked you in. And we hit it off from that moment on," Jada told People.

The mom of two also unpacked the extreme poverty she saw her friend experience. When they met, Jada says the Dear Mama hitmaker only owned "two pairs of pants and two sweaters", but he never let that stand in the way of his big dreams.

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A few years down the road and rumours of their romantic relationship were all the tabloids could go on about. It's believed the couple ended their romance in 1995 after a falling out. Just a year later, Tupac died after being shot four times in a drive-by shooting.

The Matrix star has always had deep regrets about leaving things unsaid between them. Looking back, Jada says Tupac's death was a big lesson:

"Life is too short. Do not let disagreements stand in between you and people that you love," she touchingly said.

Tupac & Madonna's secret relationship

Pop icon Madonna shocked the world in 2015 when she revealed her secret romance with Tupac. Their love brought two worlds together when the prim princess and the hip-hop artist finally locked eyes.

Opening up about their relationship during a radio interview 20 years later, Madonna told Howard Stern all the juicy details. Apparently, a 1995 TV interview went really sour for Madge after a fight with her boyfriend, Vogue reports.

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“I was dating Tupac Shakur at the time, and the thing is he got me all riled up on life in general,” she said. “So, when I went on the show, I was feeling very gangsta," the pop icon shared.

Pac's letter to Madonna

While many of Tupac's OG fans have accused the pop star of hyping up a relationship they believe to be nothing more than a fling, the rapper's candid letter to Madonna may have proven otherwise.

Written in 1995 from the walls of his prison cell, the three-page love letter mentions a quarrel the young lovers had. Published by TMZ, Pac also went on about the pressures of dating a Hollywood 'it girl' and the challenges of being an inter-racial couple.

“Please understand my previous position as that of a young man with limited experience with [an] extremely famous sex symbol, I don’t know how you feel about visiting me but if you could find it in your heart, I would love to speak face to face with you," Pac allegedly wrote.

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Lisa 'Left Eye' Lopes from TLC catches Tupac with another lady

The late Lisa Lopes, best known for her starring role in the musical trio TLC, immediately fell for Pac's magnetic charm. The two rappers met in the mid-90s through music industry events and soon hit it off.

Again, music historians were sceptical and doubt the couple's romance ever developed into anything more than a fling. However, Left Eye's friends have accused the No Scrubs hitmaker of being a particularly jealous lady friend.

One night at the club, Lisa caught Tupac talking to another lady and got her claws out real quick:

“Left Eye jumps in-between the girl and Tupac kinda like, nudging the girl out of the way. And the girl, she like, one of them petty taps, tap somebody not the shoulder like, you know, like ‘scuse me, you’re in my way… When she touched Left Eye on the shoulder, Left Eye went off," the friend told Cheat Sheet.

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The friend also shared that the two never seriously dated, due in part to Lisa's on and off relationship with NFL player Andre Rison, but remained good friends up until Pac's death in September 1996.

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Source: Briefly News

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